Issue 11, 2007

Synthesis of bitriazolyl nucleosides and unexpectedly different reactivity of azidotriazole nucleoside isomers in the Huisgen reaction

Abstract

Novel bitriazolyl nucleosides were synthesized via the Huisgen reaction, starting with 3-azidotriazole nucleoside (1). Surprisingly, its isomer, 5-azidotriazole nucleoside (1′) did not yield the corresponding Huisgen reaction products efficiently because it was rapidly reduced to amine in the presence of Cu(II)–ascorbate. The significant differences between the reactivity of these two isomers in Cu(II)–ascorbate mediated reactions are mainly due to differences in their electronic properties and steric congestion as a result of different relative positions of the azido and the ribosyl moieties.

Graphical abstract: Synthesis of bitriazolyl nucleosides and unexpectedly different reactivity of azidotriazole nucleoside isomers in the Huisgen reaction

Supplementary files

Article information

Article type
Paper
Submitted
06 Mar 2007
Accepted
23 Mar 2007
First published
25 Apr 2007

Org. Biomol. Chem., 2007,5, 1695-1701

Synthesis of bitriazolyl nucleosides and unexpectedly different reactivity of azidotriazole nucleoside isomers in the Huisgen reaction

Y. Xia, W. Li, F. Qu, Z. Fan, X. Liu, C. Berro, E. Rauzy and L. Peng, Org. Biomol. Chem., 2007, 5, 1695 DOI: 10.1039/B703420B

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